Lithium tri-s-butylborohydride → 3-(3-Methoxy-3-methylbutyl)-5-methylcyclohexanol

Participants

Reaction Conditions

Reaction Steps

A solution of lithium tri-sec-butylborohydride (267 mL of a 1M solution in tetrahydrofuran, 0.27 mol) was added to a cooled (-65° C.) solution of 3-(3-methoxy-3-methlybut-1-yl)-5-methylcyclohexan-1-one (48.6 g, 0.22 mol) dissolved in tetrahydrofuran (350 mL). The solution was stirred at 25° C. for 16 hours and was quenched by addition of sodium hydroxide (10% aqueous, 165 mL) followed by hydrogen peroxide (30% aqueous, 170 mL). Workup yielded 3-(3-methoxy-3-methylbutyl)-5-methyl cyclohexan-1-ol as a mixture of diastereoisomers (ratio 90.1:7.2:2.7), bp0.75 120°-122° C. (40.7 g). This compound and mixtures of diastereomers possess strong, tenacious, sandalwoody, musky notes. NMR(CDCl3)δ0.6 (q,1H), 0.9(d,3H), 1.0-1.1(m,2H), 1.1(s,6H), 1.2-1.3 (m,2H), 1.4-1.6(m,2H), 1.6-1.9(m,5H), 2.2 (brs,1H), 3.2(s,3H), 4.1(m,1H). IR(neat) 3400, 2975, 2925, 1460, 1385, 1365, 1210, 1090, 1015 cm-1 ; MS(m/e) 43, 73, 93, 111, 149, 167, 182, 199, 200.

Provenance & Evidence